(4-苄基哌嗪-1-基)-(1H-吲哚-3-基)甲酮 | 137643-31-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: (4-苄基哌嗪-1-基)-(1H-吲哚-3-基)甲酮
• 英文名称: (4-benzylpiperazin-1-yl)(1H-indol-3-yl)methanone
• 英文别名: (1H-indol-3-yl)[4′-(phenylmethyl)piperazin-1′-yl]methanone；(4-benzylpiperazin-1-yl)-(1H-indol-3-yl)methanone
• CAS: 137643-31-3
• 化学式: C₂₀H₂₁N₃O
• mdl: MFCD03305788
• 分子量: 319.406
• InChiKey: KGJKHWBESJPEQO-UHFFFAOYSA-N

物化性质

• 沸点：
  529.8±45.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)
• 溶解度：
  >47.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  39.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-吲哚甲酸 、 1-苄基哌嗪 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (4-苄基哌嗪-1-基)-(1H-吲哚-3-基)甲酮
  参考文献：
  名称：

  Indole-based heterocyclic inhibitors of p38α MAP kinase: designing a conformationally restricted analogue

  摘要：

  p38alpha, Mitogen Activated Protein Kinase (MAP kinase) is an intracellular soluble serine threonine kinase. p38alpha kinase is activated in response to cellular stresses, growth factors and cytokines such as interleukin-1 (IL- 1) and tumor necrosis factor alpha (TNF-alpha). The central role of p38alpha activation in settings of both chronic and acute inflammation has led efforts to find inhibitors of this enzyme as possible therapies for diseases such as rheumatoid arthritis, where p38alpha activation is thought to play a causal role. Herein, we report structure-activity relationship studies on a series of indole-based heterocyclic inhibitors that led to the design and identification of a new class of p38alpha inhibitors. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00653-x

文献信息

• Acylative Coupling of Amine and Indole Using Chloroform as a Carbonyl Group
  作者：Yuika Nishida、Norihiko Takeda、Kenji Matsuno、Okiko Miyata、Masafumi Ueda

  DOI：10.1002/ejoc.201800571

  日期：2018.8.7

  Chloroform‐mediated acylative coupling of amines and indoles has been developed. Indoles and amines in chloroform were treated with dimethylzinc in the presence of air, resulting in a three‐component acylative coupling reaction in which in‐situ generation of phosgene produces indole‐3‐carboxamides.

  已开发出氯仿介导的胺和吲哚的酰基偶联。在空气中用二甲基锌处理氯仿中的吲哚和胺，导致三组分酰基偶联反应，在该反应中原位产生的光气会生成吲哚-3-羧酰胺。
• AlMe₃-Mediated Regio- and Chemoselective Reactions of Indole with Carbamoyl Electrophiles
  作者：A. Velavan、S. Sumathi、K. K. Balasubramanian

  DOI：10.1002/ejoc.201300085

  日期：2013.5

  we report the regio- and chemoselective reactions of indole with carbamoyl electrophiles in presence of AlMe3. Indole-3-carboxamide was prepared in one-step from a reaction of indole with tertiary carbamoylimidazole in the presence AlMe3. Under conditions for the formation of an aluminium ate complex, the reaction was diverted to the indole nitrogen. Secondary carbamoyl electrophiles in the presence

  在此，我们报告了在 AlMe3 存在下吲哚与氨基甲酰基亲电试剂的区域选择性和化学选择性反应。Indole-3-carboxamide 是在 AlMe3 存在下由吲哚与叔氨基甲酰基咪唑反应一步制备的。在形成铝酸盐络合物的条件下，反应转向吲哚氮。二级氨基甲酰基亲电子试剂在 AlMe3 存在下区域特异性地产生三取代的脲。还研究了吲哚氮对酯和叔氨基甲酰基咪唑官能团的区域特异性和化学选择性。
• NOVEL PIPERAZINE CONTAINING COMPOUNDS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0922042A1

  公开（公告）日：1999-06-16
• [EN] NOVEL PIPERAZINE CONTAINING COMPOUNDS<br/>[FR] NOUVEAUX COMPOSES PIPERAZINE
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：WO1998006715A1

  公开（公告）日：1998-02-19

  (EN) Novel 3-Carboxyindole piperazine amide containing compounds, and compositions for use in therapy as anti-inflammatory agents, and inhibitors of cytokine p38/MAP kinase mediated diseases.(FR) On décrit des nouveaux composés amidés contenant 3-carboxyindole pipérazine, ainsi que des compositions utiles en thérapie en tant qu'agents anti-inflammatoires, et en tant qu'inhibiteurs des cytokines p38/MAP kinases, dans des maladies induites par celles-ci.
• Indole-based heterocyclic inhibitors of p38α MAP kinase: designing a conformationally restricted analogue
  作者：Babu J Mavunkel、Sarvajit Chakravarty、John J Perumattam、Gregory R Luedtke、Xi Liang、Don Lim、Yong-jin Xu、Maureen Laney、David Y Liu、George F Schreiner、John A Lewicki、Sundeep Dugar

  DOI：10.1016/s0960-894x(03)00653-x

  日期：2003.9

  p38alpha, Mitogen Activated Protein Kinase (MAP kinase) is an intracellular soluble serine threonine kinase. p38alpha kinase is activated in response to cellular stresses, growth factors and cytokines such as interleukin-1 (IL- 1) and tumor necrosis factor alpha (TNF-alpha). The central role of p38alpha activation in settings of both chronic and acute inflammation has led efforts to find inhibitors of this enzyme as possible therapies for diseases such as rheumatoid arthritis, where p38alpha activation is thought to play a causal role. Herein, we report structure-activity relationship studies on a series of indole-based heterocyclic inhibitors that led to the design and identification of a new class of p38alpha inhibitors. (C) 2003 Elsevier Ltd. All rights reserved.